I was talking with the other half about the car(tractor) port. She came up with the idea of attaching it directly to the existing building. After pondering that for awhile and doing some measuring, I came up with this sketch. There is no provision for the hoist as yet, but having 3 less posts to set piers for is a plus. And it would be a lot more solid this way. I could add the middle interior post and still do a 4X6 beam across for the winch to attach to. Just thought I would throw this out and see what you guys think.

You're going to run into some probs with snow. The seam where the two roofs join will have a tendency to want to leak as the snow melts from the pitched roof and goes down to the flat with all the snow on it. It will build up and try to run back. You will need to figure in some pitch and take every precaution to seal the 2 roofs. Also, the water handling for the flat roof is probably sized to the surface area, will it handle the extra water from the garage?

The car port roof isn't flat. See post 17. I plan to put a drop across the 12', not much. But it will move more of the water to the outside. Plus, with the way I am opening up the gutter drains, I don't think that will be a problem. All they had for drains before can be seen in post 27, first pic. This only had a 1/2" slot and was at only at one end. I plan to use 4 downspouts like on house guttering.

Kenny, can you cut a hole through the existing shed, just below the roof line, and frame up the wall in the existing shed, to help support your cross member beam for your winch assembly? The will help support your winch beam end, along with giving you added support to the new roof, for snow weight. At least you wouldn't see the beam framing support on your side of the work area, and it would blend in rather well with the exisiting framing on the inside of the existing shed.
When framing in your walls, I suggest framing for a large enough door on the end of the building, as well as a large enough opening on the side of the building. I have a double door opening on the side of my shed, and I really wish I would have framed another set of double doors on the end of the shed. As the collection grows, or different projects add up, you start putting thing in corners, and the next thing you know, you only have half of the original door opening available. Two sets of doors = (1) set for entering/exiting, (1) set for escaping when you can't get out the other!

The car port roof isn't flat. See post 17. I plan to put a drop across the 12', not much. But it will move more of the water to the outside. Plus, with the way I am opening up the gutter drains, I don't think that will be a problem. All they had for drains before can be seen in post 27, first pic. This only had a 1/2" slot and was at only at one end. I plan to use 4 downspouts like on house guttering.

Sorry, when I said flat, I meant no pitch. If you are incorporating a pitch, that will help, but 12" over the width of the whole thing isn't a lot... I'm not trying to say don't do it... just take precautions as best you can.

Just remember this is a used unit. Has been standing for the last 20 years, so it can handle the snow loads we have around here. Plus I am adding a third post. This last winter was the worst we have seen in a long time. Usually, one 6-8" snow a year. It is engineered to be flat across, no pitch. When it is all together, I think I could walk across it.
I won't be closing this all the way in for a while, just one end to keep snow out of there. The existing building will not be changed, as much as I like to have a big door into it. South and east will be open for now. Door on existing building faces east.
If I attached the 4X6 beam to the existing building, I would have to get 14' long. I'm not sure if I can get a 12' up there. This is still in planning, so I have time to figure out something. Just would like to use the winch I bought somehow. Running with the length, would be better. Especially the first 10', as that will be the main work area. The back 10' will be parking for the tractors.
I will be keeping all this in mind. You have given me things to think about and I thank you guys for that. It all may change again before I finally get it up.

Brought home some more goodies for the 'Tractor Port' yesterday. Approximately 110 of these:

What are you going to do with these you may ask! Well, I plan to lay them flat as close together as possible to make a work surface to put the tractors on when working under them. The 'holes' left from laying them will get cement poured into them, giving a thick, fairly smooth surface for jacking, etc. Instant (well maybe a little longer than that) floor. I have to get them unloaded from the PU and trailer this morning and stacked until I am ready to lay them. I will lay a few out and take a couple pics so you have a better idea of what I plan.

Didn't get time yet to lay out those for pics. Yesterday, while walking on the side walk looking at how much the dirt has shrank away for the drought, I noticed a piece of concrete sticking up. Grabbed the sharpshooter and proceeded to pry it out, thinking it was some more of the concrete bricks I dug out earlier. Low and behold, it was an 8"X16"X2" thick block. Probed some more next to it and found another. When all were removed from under the dirt, I had 24 of these. More floor for the 'Tractor Port'. The grass should be happier now.